The ListHunt Startup Series: Part Two

Accelerate or Die: the Techstars Experience (Part 2)

“Mentor Madness” is what they call it. It’s not a mental illness where you give unsolicited advice to strangers. It’s the first month of Techstars. The purpose is simple: expose entrepreneurs to a high volume of quality mentorship in a short period of time, hoping that insights and relationships will emerge. When we say high volume, we are talking about 40 one-on-one meetings packed into 4 weeks.

As our CEO, I took basically every meeting scheduled and came prepared with research on each person, questions to ask, and ideas on how they might be able to help. You wouldn’t always know what the schedule was in advance, so often times I was scrambling around 15 minutes beforehand Googling names for information. One wise founder even had an intern prepare a brief for each meeting and help draft follow-up emails.

The kind of mentors we met (see the list here) were top-notch technology executives and investors in Chicago. Some were highly-technical product people. Some were great at sales and marketing. And some were career finance professionals. All generously gave their time to help young startups accelerate their business. It was quite a privilege to meet all these awesome people.

Sales expert Craig Wortmann taught us to drop our one-line sales hook and then give a pregnant pause. We were making this hand motion to each other all summer when someone rambled too long.

Not every mentor meeting was going to transform the business. Sometimes you spend 30 minutes trying to explain your product and realize you still didn’t get your point across. Sometimes people like you and your vision, but they have no idea how to help you at the time. Like most things in business and life, you need a high volume of interactions to find the nuggets of gold. Even if 4 of the 40 meetings were a real hit, these winners might be critically important to your business.

We had a handful of great meetings, and I bet we would have had more if I was more prepared, if we knew what we really wanted Tribe to be. We were so green and still searching for basic answers. Were we a project management tool? No, not exactly. Were we an email tool? Kind of, but not just that. Were we truly B2B, or maybe B2C, or B2C2B? There are questions in business and in life that only you can answer for yourself.

I realized in this “Mentor Madness” that you should aim to have a clear ask whenever someone is looking to help you. I look back and feel like I wanted help with too many things (intros to customers, practice pitching investors, help with product, finding a designer), so people struggled to know where to start. I found myself walking away from meetings realizing I wasted an opportunity and didn’t have a good follow-up planned.

There’s another challenge with mentorship that goes beyond the Techstars experience and applies to anyone in a leadership role. This is the problem called “mentor whiplash.” Everyone has a unique and subjective opinion about what you should do, and if you lined up all the advice you have, there would be conflicting ideas. Usually, there is more than one right answer, and the best approach is really to be thoughtful about your choices but stay focused. We got rocked pretty badly by mentor whiplash during the first month of Techstars. For a few days, I wanted to roll up in a ball and just hide. I needed some space to soul search and figure things out, but during Techstars mentor month, no such luxury existed. If we had a glaring weakness, by god, they would find it!

It wasn’t all whiplash and madness. Our absolute best meetings were with Logan LaHive (Belly), Jessica Yagan (Impact Engine), and Justin Massa (Food Genius). They were all excited about the product and had a personal connection to what we were doing. After a great high-energy session with Justin Massa, we decided to choose him as our “Super Mentor,” which means he would meet with us weekly throughout the rest of the program. This was awesome, since Justin went through the Techstars program just a few years before and was ready to roll up his sleeves and help with product.

From our first Super Mentor meeting to the moment when Justin introduced us on stage at Demo Day, he was like one of the team: testing the app, coming up with strategies, and helping make sense of metrics each week. We will always be grateful to Justin and the dozens of mentors who helped us during that crazy, scary first month.

We learned a ton in just 4 jam-packed weeks! Like my co-founder Sam always says about mentors, “They don’t help you with the 100 things you know you need to do and aren’t doing, they just make you aware of the 500 OTHER things you didn’t even know you weren’t doing.”

August arrived and the madness faded, but the next challenge would prove even harder. For month two, we would have to apply all the lessons learned and start driving the core metrics of our business. One of these numbers, 9%, would haunt us for the next 30 days.

[…] part one of this series, “The First Day”, click here. For part two of this series, “Mentor Madness”, click here. For part three of this series, “Momentum and Metrics”, click here. For part four of this […]